Abstract
d-Ribose, d-xylose, d-arabinose, and l-arabinose have been converted in good yield into their respective diphenyl dithoacetals, 1, 5, 8, and 3. The tetraacetate 4 of 3 adopts a planar, zigzag conformation in chloroform solution, but the d- xylo analog 6 and d- ribo analog 2 adopt conformations that have no parallel 1,3-interactions of acetoxyl groups. A crystalline diisopropylidene acetal 7 was obtained from 1. On treatment with a strong base, the corresponding acetal 9 from the d- arabino derivative 8 underwent elimination of acetone to give the ketene diphenyl dithioacetal 10, characterized as its crytalline 3- p-nitrobenzoate 11 and its remarkably stable 3-methyl ether 12.
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